


Rosegarden Glory-hole Fun

by VincentVanNintendogh



Category: RWBY
Genre: Anal Sex, Bisexual Male Character, Blow Jobs, F/M, Glory Hole, Kissing, M/M, Multiple Orgasms, Semi-Public Sex, Smut, Snowballing, Teasing
Language: English
Status: Completed
Published: 2020-08-19
Updated: 2020-08-19
Packaged: 2021-03-06 03:13:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,352
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25986436
Author URL: https://archiveofourown.org/users/VincentVanNintendogh/pseuds/VincentVanNintendogh
Summary: Ruby introduces her boyfriend Oscar to the joy that they can have together in a bathroom hole with a certain special feature inside.
Relationships: Oscar Pine & Ruby Rose, Oscar Pine/Ruby Rose
Comments: 3
Kudos: 17





	Rosegarden Glory-hole Fun

**Author's Note:**

> This fic was inspired by my friend AikiYun's prompt on a mutual Discord server. Seems to be a reoccurring theme that my stories come from either Aiki's art or his prompts since 3 of 5 my works are attributed to him. Anyway, had a lot of fun with this story and wanted to capture one of our favorite ships in a very lewd and somewhat OOC moment. It should be noted that Oscar consented to all of the events and that both he and Ruby are of age (at least 18 and 19, respectively) in this story. I hope you enjoy it!

Oscar was shaking from head to toe when Ruby proposed this idea for them to do. He had never expected his girlfriend, whom he assumed to be more vanilla and innocent in terms of sex, to come up with this idea. But as he kneeled on the floor of the dingy bathroom staring at a hole in the stall the reality of the situation fully dawned upon him.

“It’s gonna be fine, Oscar.” Ruby softly spoke into his ear from behind him. “You’re gonna be a natural at this.”

She pressed her naked body into his back, her breasts pushing into him. All that both of them had on were a pair of red and green thigh highs, each matching their own color palettes. While Ruby’s made sense with her usual attire, he had agreed to wear his attire to further please his girlfriend. The stall itself was small, barely able to fit one person let alone two. Both walls of the stall had a small hole carved out of them, making it clear on what activities went on inside.

“All we need to do is wait for someone to knock on the other side of the stall. Then the fun will really begin!” Her voice carried a husky tone that struck a nerve directly causing his modest cock to twitch in response. Thoughts of whether he was actually getting excited for this began to swarm his mind. Yet he had not time to process them as they heard the bathroom door to the men’s room swing open followed by heavy footsteps approaching them. The door to the stall next to them opened and for a few seconds the only sound in the room that Oscar heard were the soft breaths of him and his girlfriend behind him.

Then, breaking the silence, three knocks came from the wall of the stall next to them. Ruby smiled as Oscar shivered in anticipation. She soothed his worries by slowly reaching down to his groin and stroking his member slowly as she gave him a kiss on the cheek. 

“Shhhh, relax, my little farm boy.” She said as she reached her other hand up to knock three times on the stall, alerting the man on the other side that what he came here for was ready and waiting. The light sound of a zipper being pulled down filled the room and a second later a large half-erect cock was pushed through the hole with Oscar’s lips lightly brushing the head. The aroma of the thick pole shoved in his face filled his nose as his mouths began to water at the sight of it. The hole was large enough for not only the cock to slip in but the two balls beneath it as well.

Ruby continued to pleasure Oscar with one hand while her other gripped the half-erect stranger’s dick, slowly bringing it to full mast right before Oscar’s eyes.

“Now, Oscar, be a good boy and please open up your slutty little mouth for me and the nice cock.” Oscar did as his girlfriend told him to and started to suck the head of the thick member. He began tasting the salty pre cum cumming from the slit and started to swirl his tongue around it to collect the liquid treat. Groans could be heard from the other side of the wall as an indication that his partner was enjoying his ministrations. 

“See, Oscar, he likes it. Now, why don’t you show him what I taught you.”

With his confidence now getting a boost, he began to swirl his tongue along the underside of the cock while slowly inching his way down until the entire member was touching the back of his throat. With his lips making it all the way to his new lover’s groin, he left a sloppy kiss upon it as he began to pull back to the tip to repeat his motions. As his head bobbed back and forth on the cock, it’s owner decided it was time to make his own moves. Just as Oscar reached the tip again he felt the cock thrust itself all the way to the back of his throat, taking him by surprise and knocking the wind out of him. He was about to pull off when Ruby took her free hand held onto the back of Oscar’s head, forcing him to stay in place.

“It’s okay, Oscar. Breathe through your nose, just like we practiced. Make sure he enjoys it.” She said breathily.

Oscar again complied with his girlfriend’s request and slowly began inhaling through his nose as hot exhales onto the cock caused it to twitch in his mouth. After ten seconds of holding in the back of his throat, Ruby relented and allowed Oscar to pull back so that just the tip was in his mouth. He took this as a sign to resume his previous pace and began to drag his way up and down on the cock, coating it in saliva.

It wasn’t long before the groans on the other side wall began to get more frantic as the cock in his mouth began to twitch. Ruby realized what was coming before Oscar and gently cupped the strangers balls in her hand, tenderly rolling them around as they began to tense in anticipation. With her other hand she firmly tightened her grip upon Oscar’s cock.

“Now remember these two rules, my little farm boy; do not cum until I say so and do not swallow the nice treat you are about to get, okay?” While her words were soft, her hold on his cock was not, serving as a warning to follow her orders. Oscar nodded his head as quickly as he could, holding back his own orgasm that was building. 

It wasn’t long after before the cock reached the end it had long sought. Oscar pulled his head back so his lips once again suckled on the head while it rested upon his tongue. The thick member began to erupt rope after rope of his cum into his mouth. Oscar’s cheeks began to bulge as he held onto the prized treat, tasting it’s bittersweet flavor upon his tongue. After a few more shots, the dick began to soften in his mouth and finally pulled out, covered in drool and leaking cum onto the floor. It finally retreated back into the hole and the shuffling of pants could be heard as the man redressed and began to walk out of the stall, saying a small ‘thanks’ as he departed.

Ruby grabbed Oscar by his chin and captured his lips with her own, her tongue forcing its way into his mouth where it began to scoop out the cum Oscar was holding. She began to snowball the cum back and forth with her boyfriend, deepening the kiss and debauchery in the process. After she had her fill of cum she parted from Oscar’s lips, leaving them only connected by a thin line of saliva and cum, which was severed with a quick flick of her tongue.

“Mhmmm, tasty.” Ruby declared. “You’ve been very good so far. Now, swallow what’s left of your treat.”

Oscar did so, feeling the creamy seed flow down his throat, savoring the taste and flavor.

“That’s my good boy. I’m sure you enjoyed the taste, didn’t you?”

Oscar nodded in response, averting his eyes to the floor to avoid her cheshire grin at his flustered features.

“Now, we wait for a few other ‘little’ friends to show up and then we can go on to the main event. Does that sound fun, my little farm boy?”

“Y-Yes, Ruby. It sounds… exciting.” Oscar’s voice showcased his anxiety, yet, also was layered with anticipation of his next ‘friend’ for the day. He wouldn't have to wait long, for three more knocks came on the side of the stall. Apparently, another man had entered while they were talking. Ruby again knocked back three times to let the man know it was ‘occupied’.

Just like before, the sound of fly being pulled down precluded a thick cock being pushed through. However, this one was not destined for a simple blowjob. Ruby helped usher Oscar onto his feet and slowly turned him so that he was facing her while his tight and lightly freckled ass was turned to the stall. Ruby gave him a quick peck on the lips and backed him up to the wall. The stranger's member was already pulsating and eager for a hole, one it would soon get in the form of Oscar's tight pucker.

Slowly, Oscar was backed onto the thick member until it pressed right up on his hole and waited to enter. Oscar was on edge as the seconds came to a standstill. Sure he was no anal virgin, Ruby had sought to take that from him with her dark red strap-on many times back in their bedroom. However, this was the first real penis that Oscar would have inside of him. He could feel the textured difference and heat pulsating from the member, as well as pre-cum leaking from the tip, ready to enter him.

It seemed that it wouldn’t be long before he found out what it truly felt like, as in a matter of seconds the cock thrusted into his asshole. He gasped in pain and pleasure as it hilted inside of him. His eyes were firmly locked with Ruby’s, watching as she still wore her grin on her face.

“How does it feel to be filled by a real cock? How does it feel to be on the other end of the act, my love?” Ruby’s tone carried a hint of playfulness in it. She was thoroughly enjoying watching Oscar get fucked as the cock began to pull back, only to slam right back in again. Though, he seemed to be enjoying it more than she was if his O-face and eyes rolling up in his head at being filled was any indication. The pace the stranger set was fast and brutal, though Oscar felt only waves of pleasure as he was being used as fuck hole for the strangers cock.

While Oscar was having his fun, Ruby had her own method of entertainment waiting for her. What Ruby was planning was to make use of the gloryhole on the opposite door while Oscar was getting plowed like the farm boy he is. As luck would soon have it, another man had entered the bathroom and went to the third stall on the other side of their own. No knocks were needed for the sounds of flesh against flesh and Oscar’s balls being slapped by the stranger’s own pair echoing through the room. The newcomer could tell that the fun had already begun. Ruby slowly backed up from Oscar, maintaining eye contact and watching him in his state of bliss the whole time.

As soon as she reached the opposite end of the stall, she felt a rod poke at her backside. Looking down, she took note of the member that was seeking her backdoor. It was larger than the one Oscar had in him, though only just. Like the other stranger’s cock it was already fully erect and wanting nothing more than a hole to fill. Ruby happily obliged the stranger by lowering her fit and plump ass onto the member, enveloping it in her tight hot hole.

Thus, both of the young lovers were now being fucked in tight holes simultaneously. Ruby set her pace on bouncing up and down on her cock to match that of the stranger fucking Oscar. She wanted them both to be thoroughly fucked together simultaneously in the long evening ahead of them in this stall.

While Ruby’s ass was just beginning to get fucked, Oscar’s has been taking a pounding for minutes, though to him the blissful experience seemed to be going on for hours now. The cock inside him began to quicken it’s pace, it’s balls slapping harder against his own. Oscar himself felt a tightening building up in his groin. He had been on edge ever since Ruby’s handjob while he served the other stranger on his knees. His orgasm was begging to release, however Ruby’s rule of refraining from cumming acted as a mental cock ring that was staving off his release.

Oscar, fearing he was close, looked to Ruby with pleading eyes and an open mouth, groaning in pleasure.

“R-Ruby go-nna cum soooon! Please!” Oscar begged for mercy, hoping for permission to allow for his release.

Ruby smiled as she bounced up and down on her new friend’s cock. Meeting his thrusts with her own motions as her ass cheeks jiggled as she went up and down. She considered teasing him and denying his request. The pleasure she would get looking into his eyes as he was denied orgasm again and forced to hold back until she allowed it. Just the thought of it got her pussy wetter than before. She brought a hand down and slowly traced her outer lips, circling around them as she closed her eyes in pleasure to debate Oscar’s request. ‘He has been such a good boy,’ she thought as the middle and ring finger entered her pussy, going in and out, matching the pace of the cock she was riding. An idea flashed through her mind on how to give him his desires while getting her own form of pleasure as well.

“My dear little farm boy, you may finish when I say so. When you do, you must do one more task after you are finished. You will eat me out and hold onto what I give you. Do you understand?”

Oscar’s mind was ablaze with lust and could barely make out what she had said. He made out what the caveat to his orgasm was and hastily agreed as he felt the cock within him leaking more and more pre-cum, lubing his ass further as it clenched down upon it. He vigorously nodded his head as an indication that he would do anything she asked.

“Good boy.”

The cock inside of him hit deep upon it’s quickened thrusts, finding a bundle of pleasure that made Oscar see stars for a split second. He was at his limit as his knees buckled barely keeping him standing.

“Oscar.” Ruby stated in a serious tone. He lifted his head to stare directly into her eyes.

“Cum.”

With that single word and a final hilt upon his prostate from the cock in him Oscar ejaculated upon the floor. Rope after rope of build up spurted from his penis, as too did the cock in his ass begin to fill him up with its own seed. For the few seconds it lasted, Oscar was in heaven. After a few final spurts his member went limp, as too did his knees. He slowly sank to the floor, releasing his tight hold on the stranger with a soft pop as copious amounts of fluid began to leak from his asshole. The stranger’s member leaked a few strands upon the floor before softening and slowly retreating through the hole, just like the last cock.

Ruby smirked as she watched her boyfriend collapse in ecstasy on the floor. The pleasure watching him finish was more than the cock inside her could ever hope to provide. However, now that her lover had his orgasm, it was her turn now.

“Good boy, I am sure you enjoyed that! But now, you have to fulfill your end of the deal.” Ruby brought the fingers that were inside of her up into her mouth, licking them clean of her juices.

Oscar slowly lifted his head off the floor and gawked at the sight. He began to recompose himself until he was able to crawl to his hands and knees towards her dripping pussy. Once in front of her, he braced his hands upon her legs and gave her a long lick from the bottom of her cunt to the top of her neatly trimmed pubes. He would continue this process, hindered only by the fact that Ruby continued to ride the stranger’s cock in her ass as well as match his thrusts in her. 

Oscar began another lick from top to bottom, this time dipping low enough to reach her taint and work his tongue towards her dick-filled asshole. He began to drag his tongue across the cock, lubricating it with his saliva. He tasted the pre-cum mixed alongside it and began to savor the taste. After a few more seconds of indulging the stranger, he made his way back up to Ruby’s wet entrance and squirmed his tongue inside of her.

Ruby squealed in pleasure as she was filled from both ends. She reveled in the depravity she had gotten her boyfriend to perform, willingly and of his own volition and enjoyment, no less. The high she was getting from the cock and tongue thrusting inside of her was taking her to the end in a masterful way. It wasn’t long before she closed her eyes in bliss as she began to feel her climax building. She brought one hand up to her mouth and bit on her index finger to silence her moans. Her other hand reached out for Oscar’s, which he gladly gave, as they interlaced their fingers and mesh their hands together, palm against palm. That intimate act was all it took as the dam broke in her as she came.

With her walls tightening around Oscar’s tongue he tasted her sweet flavor secreting from them. With all the cookies she ate, he knew that he would expect nothing less from Ruby. However, as he was thinking of her taste, a clear fluid began to squirt out in thin shots into his mouth. He held on to each one in his cheeks, for his girlfriend did not tell him to swallow yet.

The man on the other end of her was also at his peak. If Ruby’s front walls felt tight around Oscar’s tongue, then her ass was like a vice, milking the cum out of the cock. As Ruby was experiencing her orgasm the man had just reached his, filling her ass with his cum. After a few more weak thrusts, what was left of the man’s orgasm dribbled out as he pulled out of Ruby’s ass and retreated back through the hole. Soon, the sounds of footsteps leaving filled the room until the door to the bathroom opened and he was gone. Ruby and Oscar remained alone in the bathroom, both of them filled to the brim with cum.

Oscar pulled away from Ruby, his cheeks lightly puffing from holding her fluids in his mouth and awaited her commands. Instead of being ordered to swallow, Ruby kneeled in front of him and took his chin in her hand gazing right in his eyes. She closed the distance between them and seized his lips with her own just like before. She moved her tongue into his mouth to gather some dollops of her own essence. They shared the sweet treat together before Ruby pulled back and both swallowed the remnants of her orgasm.

“You have been a very good boy so far. When we get home, I’ll make sure you get another special pounding from ‘Mini Crescent Rose’! If you can last against that, I’ll let you top after.” Ruby dangled the prize of being in charge in front of his face. Granted, he would have to endure another pounding, this time from her red strap-on. Still, it was worth it.

Before he could respond, three more knocks came from Oscar’s side of the stall. He turned to see that like all the times before, a large cock slipped through the hole.

Ruby smiled at this development and gave Oscar a quick peck on the cheek. “All of that comes after we finish here. Which, if we are lucky, won’t be for a while, my dear farm boy.” 

With that statement both lovers got back to pleasuring the members that arrived for the rest of the evening.


End file.
